Dicyclohexylcarbodiimide → (4S)-3-{[(4-Methoxybenzyl)thio]acetyl}-4-phenyl-1,3-oxazolidin-2-one

HRID 1366313Notes

Reaction equation

HRID 1366313 reaction equation
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]([CH2:7][S:8][CH2:9][C:10]([OH:12])=O)=[CH:5][CH:4]=1.C1(N=C=NC2CCCCC2)CCCCC1.[C:30]1([C@H:36]2[CH2:40][O:39][C:38](=[O:41])[NH:37]2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][S:8][CH2:9][C:10]([N:37]2[C@@H:36]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:40][O:39][C:38]2=[O:41])=[O:12])=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 7304242-Oxazolidinone, 4-phenyl-, (4S)-HCID 958072[(4-Methoxybenzyl)sulfanyl]acetic acid

Product 1

HCID 59326632(4S)-3-{[(4-Methoxybenzyl)thio]acetyl}-4-phenyl-1,3-oxazolidin-2-one

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

[(4-Methoxybenzyl)thio]acetic acid (1.3 g, 6.1 mmol) was dissolved in dry CH2Cl2 (40 ml) and given 0° C. N,N′-Dicyclohexylcarbodiimide (DCC, 6.1 g, 6.1 mmol) and 4-(dimethylamino)pyridine (DMAP, 1.6 g, 12.9 mmol) were added and the mixture was stirred for 30 minutes. (S)-(+)-4-Phenyl-2-oxazolidinone (1.0 g, 6.1 mol) was added and the mixture was stirred at room temperature for 24 hours. The mixture was filtrated, concentrated under reduced pressure and purified by flash-chromatography (Hex:EtOAc 8:2 then 1:1). This afforded the title compound as a white solid.

Workup

  1. customgiven 0° C
  2. stirringthe mixture was stirred at room temperature for 24 hours
  3. filtrationThe mixture was filtrated
  4. concentrationconcentrated under reduced pressure
  5. custompurified by flash-chromatography (Hex

Sources & evidence

ORD record
ord-bb505d1767c846658fcd5aab5d3c7278
Source dataset
uspto-grants-2011_02
Patent number
US07893048B2

Reaction notes

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